ethyl 2-oxo-3-(triphenyl-$l^{5}-phosphanylidene)propanoate

• ChemBase ID: 74863
• Molecular Formular: C23H21O3P
• Molecular Mass: 376.384801
• Monoisotopic Mass: 376.12283116
• SMILES: P(=CC(=O)C(=O)OCC)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: CCOC(=O)C(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C23H21O3P/c1-2-26-23(25)22(24)18-27(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h3-18H,2H2,1H3
• InChIKey: OQLOPRPWPANPIE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-oxo-3-(triphenyl-$l^{5}-phosphanylidene)propanoate; ethyl 2-oxo-3-(triphenyl-λ^5-phosphanylidene)propanoate
• IUPAC Traditional name: ethyl 2-oxo-3-(triphenyl-$l^{5}-phosphanylidene)propanoate; ethyl 2-oxo-3-(triphenyl-λ^5-phosphanylidene)propanoate
• Synonyms: Ethyl (triphenylphosphoranylidene)pyruvate; [2-(Ethoxycarbonyl)-2-oxoethylidene]triphenylphosphorane; 2-Ethoxycarbonyl-2-oxoethylidenetriphenylphosphorane; NSC 647346; [(Carboxycarbonyl)methylene]triphenylphosphorane ethyl ester; Ethyl (triphenylphosphoranylidene)pyruvate; (三苯基膦)丙酮酸乙酯

Database IDs

• CAS Number: 13321-61-4
• MDL Number: MFCD00208428
• PubChem SID: 162039781; 24873999
• PubChem CID: 372288

CALCULATED PROPERTIES

• Acid pKa: 18.987816
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.7122
• LogD (pH = 7.4): 6.7122
• Log P: 6.7122
• Molar Refractivity: 108.5437 cm^3
• Polarizability: 42.504253 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 175 °C (dec.)(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%
• Linear Formula: (C6H5)3P=CHCOCO2C2H5

DETAILS

Sigma Aldrich - 518093

Packaging
25 g in glass bottle
Application
Reactant for:
• Wittig condensation1
• Chemoenzymic preparation of hexafluoroleucine and tetrafluoroleucine2Reactant for synthesis of:
• Ahiral and chiral cyclic dehydro-α-amino acid derivatives through nucleophilic addition3
• Peptidyl α-keto-based inhibitors of cruzain4
• Deoxyfluoro-L-arabinofuranosyl triazole nucleoside derivatives with antiviral activity5
• Anti-human immunodificiency virus analogs6